US20020055566A1 - Water-based formulations with fungicidal action - Google Patents
Water-based formulations with fungicidal action Download PDFInfo
- Publication number
- US20020055566A1 US20020055566A1 US09/552,044 US55204400A US2002055566A1 US 20020055566 A1 US20020055566 A1 US 20020055566A1 US 55204400 A US55204400 A US 55204400A US 2002055566 A1 US2002055566 A1 US 2002055566A1
- Authority
- US
- United States
- Prior art keywords
- aqueous systems
- binders
- hydrolysis
- water
- active compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 title description 2
- 238000009472 formulation Methods 0.000 title 1
- 230000000855 fungicidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 239000011230 binding agent Substances 0.000 claims abstract description 17
- 229920000180 alkyd Polymers 0.000 claims abstract description 14
- 230000007062 hydrolysis Effects 0.000 claims abstract description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 7
- 239000008158 vegetable oil Substances 0.000 claims abstract description 7
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 claims description 7
- NCDBYAPSWOPDRN-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]sulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)F)C(=O)C2=C1 NCDBYAPSWOPDRN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005789 Folpet Substances 0.000 claims description 3
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 claims description 3
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 2
- 239000005745 Captan Substances 0.000 claims description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 2
- 229940117949 captan Drugs 0.000 claims description 2
- -1 compound compounds Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical class 0.000 claims 1
- 206010061217 Infestation Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- 239000013011 aqueous formulation Substances 0.000 abstract description 2
- 239000003973 paint Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000003373 anti-fouling effect Effects 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003171 wood protecting agent Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
Definitions
- the present specification relates to storage-stable aqueous formulations which in addition to hydrolysis-sensitive active compounds comprise special binders for stabilizing the active compounds.
- trihalogenomethylthio compounds such as dichlofluanid, tolylfluanid, fluorfolpet and folpet is based on the ability of the N—S bond to open in order subsequently to react nucleophilic groups (e.g. SH groups).
- aqueous systems comprising at least one hydrolysis-sensitive active compound in combination with binders which consist of alkyd resins based on vegetable oils and/or acrylate dispersions and which in aqueous systems have a pH ⁇ 7.
- Active compounds sensitive to hydrolysis are, in particular, fungicides, bactericides and insecticides which in acidic, neutral and especially alkaline systems have a half-life of a few minutes to six months.
- Such active compounds are, in particular, compounds containing a functional group —N—S—CCl 2 X, where X preferably represents fluorine, chlorine or CHCl 2 .
- Hydrolysis-sensitive active compounds for the purposes of the invention are, in particular, folpet, captan and captafol and, preferably, dichlofluanid, tolylfluanid and fluorfolpet.
- Binders for the purposes of the invention are alkyd resins and acrylate dispersions, which may also, optionally, be present in copolymeric form and which have the characteristic that in aqueous solutions or emulsions they have a pH ⁇ 7, in particular ⁇ 5, preferably ⁇ 3.
- alkyd/maleic anhydride copolymers alkyd/modified linseed oil, alkyd resins, alkyd resin/soya oil/linseed oil in combination with acrylate dispersion.
- the aqueous systems of the invention, or ready-to-use compositions contain preferably from 0.001 to 90, in particular from 0.01 to 50, more preferably from 0.1 to 5, with particular preference from 0.1 to 2 per cent by weight of active compound and preferably from 3 to 80, in particular from 5 to 50 and, more preferably, from 5 to 30 per cent by weight of binder.
- aqueous systems are water-based paints such as, in particular, emulsion paints and antifouling paints and also, preferably, wood preservatives such as, in particular, wood preservative varnishes and primers.
- Aqueous systems optionally include constituents which are common for—in particular—wood preservative varnishes, emulsion paints and antifouling paints, such as pigments, dyes, auxiliaries, binders, emulsifiers, dispersants and further active compounds such as fungicides, insecticides and/or bactericides not sensitive to hydrolysis.
- constituents which are common for—in particular—wood preservative varnishes, emulsion paints and antifouling paints such as pigments, dyes, auxiliaries, binders, emulsifiers, dispersants and further active compounds such as fungicides, insecticides and/or bactericides not sensitive to hydrolysis.
- the aqueous systems of the invention have the advantage over the known systems that the active compounds are stable for long periods against hydrolysis and decomposition, both in an acidic and in a neutral medium.
- Tolylfluanid (TF) is incorporated into various water-based wood preservatives with stirring. The samples are tested for their storage stability at room temperature. The amount of active compound in the samples is measured by means of HPLC.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
The invention relates to storage-stable aqueous formulations containing at least one hydrolysis-sensitive active compound in combination with binders consisting of an alkyd resin based on vegetable oils and/or acrylate dispersions and having a pH≦7.
Description
- The present specification relates to storage-stable aqueous formulations which in addition to hydrolysis-sensitive active compounds comprise special binders for stabilizing the active compounds.
- Their sensitivity to hydrolysis imposes conditions on the suitability of many broad-spectrum fungicides for use in water-based systems.
- The mode of action of, for example, trihalogenomethylthio compounds such as dichlofluanid, tolylfluanid, fluorfolpet and folpet is based on the ability of the N—S bond to open in order subsequently to react nucleophilic groups (e.g. SH groups).
- The half-life of the majority of these compounds in aqueous systems is a few minutes at alkaline pH levels (about pH 9), in the neutral range (about pH 7) a few hours, and in the acidic range (about pH 4) a few days.
- Their use in water-based, so-called ready-to-use wood preservation varnishes and primers, emulsion paints and antifouling paints is therefore not an option owing to the short shelf life, which derives from the instability of the fungicides.
- Surprisingly and totally unexpectedly it has now been found that active compounds sensitive to hydrolysis can be stabilized by using specific binder systems.
- The specification therefore provides aqueous systems comprising at least one hydrolysis-sensitive active compound in combination with binders which consist of alkyd resins based on vegetable oils and/or acrylate dispersions and which in aqueous systems have a pH≦7.
- Active compounds sensitive to hydrolysis are, in particular, fungicides, bactericides and insecticides which in acidic, neutral and especially alkaline systems have a half-life of a few minutes to six months.
- Such active compounds are, in particular, compounds containing a functional group —N—S—CCl 2X, where X preferably represents fluorine, chlorine or CHCl2.
- Hydrolysis-sensitive active compounds for the purposes of the invention are, in particular, folpet, captan and captafol and, preferably, dichlofluanid, tolylfluanid and fluorfolpet.
- Binders for the purposes of the invention are alkyd resins and acrylate dispersions, which may also, optionally, be present in copolymeric form and which have the characteristic that in aqueous solutions or emulsions they have a pH≦7, in particular ≦5, preferably ≦3.
- Examples of preferred binders which may be mentioned are as follows:
- alkyd/maleic anhydride copolymers, alkyd/modified linseed oil, alkyd resins, alkyd resin/soya oil/linseed oil in combination with acrylate dispersion.
- Both the active compounds and the binders are known and are commercially available.
- The aqueous systems of the invention, or ready-to-use compositions, contain preferably from 0.001 to 90, in particular from 0.01 to 50, more preferably from 0.1 to 5, with particular preference from 0.1 to 2 per cent by weight of active compound and preferably from 3 to 80, in particular from 5 to 50 and, more preferably, from 5 to 30 per cent by weight of binder.
- Preferred examples of aqueous systems are water-based paints such as, in particular, emulsion paints and antifouling paints and also, preferably, wood preservatives such as, in particular, wood preservative varnishes and primers.
- Aqueous systems optionally include constituents which are common for—in particular—wood preservative varnishes, emulsion paints and antifouling paints, such as pigments, dyes, auxiliaries, binders, emulsifiers, dispersants and further active compounds such as fungicides, insecticides and/or bactericides not sensitive to hydrolysis.
- The aqueous systems of the invention have the advantage over the known systems that the active compounds are stable for long periods against hydrolysis and decomposition, both in an acidic and in a neutral medium.
- The invention is elucidated further by the following examples. The invention is not restricted to the examples. In the text below, percentages are by weight.
- Tolylfluanid (TF) is incorporated into various water-based wood preservatives with stirring. The samples are tested for their storage stability at room temperature. The amount of active compound in the samples is measured by means of HPLC.
- The table below reports the results:
TABLE 1 % TF % TF, storage at RT Ex.- Binder pH of after 1 2 3 9 12 No % Description B theor. prep. mth. mth. mth. mth. mth. 1 16.5 Alkyd/soya/linseed oil + 2 0.74 0.72 0.80 0.69 0.69 0.67 0.69 acrylate dispersion 2 16.5 Alkyd 3.5-5 0.74 0.74 0.97 0.75 0.64 0.63 0.62
Claims (10)
1. Aqueous systems comprising at least one hydrolysis-sensitive active compound in combination with binders which consist of alkyd resin based on vegetable oils and/or acrylate dispersions and have a pH≦7.
2. Aqueous systems according to claim 1 , in which the binders have a pH≦5.
3. Aqueous systems according to claim 1 , in which the binders have a pH≦3.
4. Aqueous systems according to claim 1 which comprise as active compound compounds having a functional group N—S—CCl2X, where X represents halogen or optionally halogen-substituted C1-C4-alkyl.
5. Aqueous systems according to claim 1 , which comprise as active compounds folpet, captan, captafol, dichlofluanid, tolylfluanid and/or fluorfolpet.
6. Use of binders which consist of alkyd resin based on vegetable oils and/or acrylate dispersions and have a pH≦7 in water for stabilizing hydrolysis-sensitive active compounds in aqueous systems.
7. Use of binders which consist of alkyd resin based on vegetable oils and/or acrylate dispersions and have a pH≦7 in water in combination with hydrolysis-sensitive active compounds for protecting aqueous systems against microbial infestation.
8. Use according to one of claims 6 and 7, characterized in that the aqueous systems have a pH≦5.
9. Binders comprising alkyd resin based on vegetable oils and/or acrylate dispersions having a pH≦7 in water in combination with hydrolysis-sensitive active compounds.
10. Method of stabilizing hydrolysis-sensitive active compounds in aqueous systems, characterized in that the aqueous systems are admixed with binders consisting of alkyd resin based on vegetable oils and/or acrylate dispersions and having a pH≦7 in water.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19918730A DE19918730A1 (en) | 1999-04-24 | 1999-04-24 | Water-based formulations with fungicidal activity |
| DE19918730.4 | 1999-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20020055566A1 true US20020055566A1 (en) | 2002-05-09 |
Family
ID=7905783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/552,044 Abandoned US20020055566A1 (en) | 1999-04-24 | 2000-04-19 | Water-based formulations with fungicidal action |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20020055566A1 (en) |
| EP (1) | EP1046337B1 (en) |
| JP (1) | JP5088983B2 (en) |
| KR (1) | KR20010014703A (en) |
| AT (1) | ATE290780T1 (en) |
| CZ (1) | CZ295971B6 (en) |
| DE (2) | DE19918730A1 (en) |
| DK (1) | DK1046337T3 (en) |
| EE (1) | EE04512B1 (en) |
| HU (1) | HUP0001559A3 (en) |
| NO (1) | NO323351B1 (en) |
| PL (1) | PL196416B1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113399A (en) * | 1961-04-05 | 1963-12-10 | Cargill Inc | Protected seed |
| US5248450A (en) * | 1989-03-02 | 1993-09-28 | Desowag Materialschutz Gmbh | Composition for use an an agent or concentrate for the preservation of wood or wood materials |
| US5972971A (en) * | 1993-06-21 | 1999-10-26 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
| US5990143A (en) * | 1991-09-19 | 1999-11-23 | Bayer Aktiengesellschaft | Water-based, solvent- and emulsifier-free microbicidal active compound combination |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004319A1 (en) * | 1980-02-06 | 1981-08-13 | Desowag-Bayer Holzschutz GmbH, 4000 Düsseldorf | WOOD PROTECTIVE CONCENTRATE AND PRODUCT MADE THEREOF FOR THE PRESERVATION OF WOOD AND WOOD MATERIALS |
| DD153888A1 (en) * | 1980-06-04 | 1982-02-10 | Horst Kirk | BIOZIDE-EQUIPPED WAESSER DISPERSION PAINTINGS |
| DE3414244C2 (en) * | 1984-04-14 | 1994-02-10 | Desowag Materialschutz Gmbh | Wood preservative paint, preferably wood preservative paint |
| JPH02279602A (en) * | 1989-04-19 | 1990-11-15 | Takeda Chem Ind Ltd | Termite-proofing aqueous suspension formulation |
| DE3927806A1 (en) * | 1989-08-23 | 1991-04-11 | Desowag Materialschutz Gmbh | MEDIUM OR CONCENTRATE FOR PRESERVING WOOD OR WOOD MATERIALS |
| DE4209939A1 (en) * | 1992-03-27 | 1993-09-30 | Desowag Materialschutz Gmbh | Emulsifier-free, water-dilutable concentrate or means for preserving wood and wood-based materials |
| US6017955A (en) * | 1995-06-07 | 2000-01-25 | Troy Technology Corporation, Inc. | Method of stabilizing biocidal compositions of haloalkynyl compounds |
| JPH0977609A (en) * | 1995-09-12 | 1997-03-25 | Dainippon Ink & Chem Inc | Reducing agent against chemical injury caused by herbicide and reduction of growth hindrance against lawn grass by herbicide |
| WO1999039886A1 (en) * | 1998-02-06 | 1999-08-12 | Lonza Ag | Protective agents for wood |
-
1999
- 1999-04-24 DE DE19918730A patent/DE19918730A1/en not_active Withdrawn
-
2000
- 2000-04-07 KR KR1020000018166A patent/KR20010014703A/en not_active Application Discontinuation
- 2000-04-11 EE EEP200000066A patent/EE04512B1/en not_active IP Right Cessation
- 2000-04-12 DE DE50009754T patent/DE50009754D1/en not_active Expired - Lifetime
- 2000-04-12 AT AT00107901T patent/ATE290780T1/en active
- 2000-04-12 DK DK00107901T patent/DK1046337T3/en active
- 2000-04-12 EP EP00107901A patent/EP1046337B1/en not_active Expired - Lifetime
- 2000-04-14 HU HU0001559A patent/HUP0001559A3/en unknown
- 2000-04-14 JP JP2000113180A patent/JP5088983B2/en not_active Expired - Fee Related
- 2000-04-19 NO NO20002071A patent/NO323351B1/en not_active IP Right Cessation
- 2000-04-19 US US09/552,044 patent/US20020055566A1/en not_active Abandoned
- 2000-04-21 PL PL339851A patent/PL196416B1/en not_active IP Right Cessation
- 2000-04-21 CZ CZ20001488A patent/CZ295971B6/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113399A (en) * | 1961-04-05 | 1963-12-10 | Cargill Inc | Protected seed |
| US5248450A (en) * | 1989-03-02 | 1993-09-28 | Desowag Materialschutz Gmbh | Composition for use an an agent or concentrate for the preservation of wood or wood materials |
| US5990143A (en) * | 1991-09-19 | 1999-11-23 | Bayer Aktiengesellschaft | Water-based, solvent- and emulsifier-free microbicidal active compound combination |
| US5972971A (en) * | 1993-06-21 | 1999-10-26 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0001559A2 (en) | 2001-01-29 |
| JP5088983B2 (en) | 2012-12-05 |
| DK1046337T3 (en) | 2005-05-17 |
| DE50009754D1 (en) | 2005-04-21 |
| HUP0001559A3 (en) | 2002-03-28 |
| PL339851A1 (en) | 2000-11-06 |
| EE04512B1 (en) | 2005-08-15 |
| NO20002071D0 (en) | 2000-04-19 |
| CZ295971B6 (en) | 2005-12-14 |
| EP1046337A2 (en) | 2000-10-25 |
| EE200000066A (en) | 2000-12-15 |
| HU0001559D0 (en) | 2000-06-28 |
| NO323351B1 (en) | 2007-04-02 |
| EP1046337B1 (en) | 2005-03-16 |
| PL196416B1 (en) | 2007-12-31 |
| CZ20001488A3 (en) | 2000-12-13 |
| KR20010014703A (en) | 2001-02-26 |
| NO20002071L (en) | 2000-10-25 |
| ATE290780T1 (en) | 2005-04-15 |
| EP1046337A3 (en) | 2001-04-18 |
| JP2000336006A (en) | 2000-12-05 |
| DE19918730A1 (en) | 2000-10-26 |
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